Today I’m continuing my story of how I went from corporate sales professional to freelance writer — and to a combination of freelance writer and coach/trainer.

This is a departure from the type shows that I’ve been publishing. But I’m constantly asked about my business, how I spend my time, where my income comes from and how I got to where I am today.

I’ve addressed these questions individually and in different training episodes I’ve published. But I’ve never told my full business-launch story in detail. And I thought this podcast format would be the ideal way to do that.

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes or on Stitcher to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Critical Mass

By the fall of 2006, I had critical mass in my business. I realized that I could afford to let go off the “prospecting accelerator” for a bit. Approximately 75% of my work was coming to me from existing/past clients and/or word of mouth, referrals and inquiries from people who found my site.

Because I had built my business on the side for more than two years, I had a very smooth transition. There was no gap in income. If anything, my income was going up.

During my first full year freelancing full time, I grossed more than $163,000. It was NOT easy. I worked my tail off and taken massive action over the past two years. And I didn’t want to turn down any work for fear that the “well” would dry off.

But it was fun! I was still riding the high of being out on my own. I felt a real sense of joy and pride knowing that I was “eating what I killed/grew.”

First 18 months freelancing full time felt this way — crazy-busy and sometimes stressful, but also very joyful and fulfilling.

An Itch to Start Something New

It was late 2007 or so that I began to get an itch; I felt like I needed a new project; something to help me grow further. Over the years, I’ve found that I come alive when I’m building something, not when it’s stable. I like building, growing. Once it’s repetitive and systemized, I look for the next thing.

I had documented what I did over the last three years, and I wanted to help others who were in the same boat. My main motivation was NOT money. It was a sense of creating something new and exciting.

I also wanted to test the passive income waters. The concept of passive income had intrigued me for a long time. (Side note: There’s very little that’s “passive” in these ventures; but that’s a topic for another podcast.)

So I carved out the first two weeks of January 2008 to write that book. I launched it in February/March, and it was a huge success!

Losing Focus

With the success of the eBook, a weird combination of things began to happen. I was in awe about how well the eBook had done. I have to admit that I had caught the passive income bug, and I couldn’t wait to create my next product.

Here again, it wasn’t so much a money thing. It’s just that I had found my next challenge — creating something new. More important, I had valuable information to share that would help many people.

This is also around the time when I teamed up with Steve Slaunwhite and Pete Savage to create the “Wealthy Freelancer” blog.

But during the spring of that year (2008), while I was busy dreaming up new products and ideas, planning and launching the blog, my prospect inquires began to dry up slowly as the economy start taking a nosedive!

Then I lost a couple of clients over the next few months, including my biggest client, which represented nearly 50% of my income at the time. And by June, things were getting a bit scary. The eBook wasn’t really a big income producer. It was the equivalent of a small client.

Big mistake: I had lost my biggest clients AND I hadn’t worked to replace them with active prospecting. Bad idea!

This created a downward spiral of negative emotions and discouragement. It showed when I talked to prospects, which repelled then, which made me feel even worse, and so on.

I had been working on another product also on the topic of making a leap into full-time freelancing. I thought it would do well. But it flopped … in a big way!

Key lesson: It’s OK to invest some of your time, energy and resources on side projects. But just like with an investment portfolio, you don’t want to invest 80% of your capital on speculative ventures — especially when most of your income comes from the more conservative investments!

It’s Darkest and Coldest Before Dawn

In Oct 2008, I received an email from someone who had once worked for my best client. She was at a new company and wanted me to meet their new VP of marketing. I wasn’t expecting much out of that meeting, but it went incredibly well.

Three weeks later, I had a signed contract for $19,000+ of work … with much more to follow.

Key lessons: Stay focused and be smart about the risks you take. And when the chips are stacked against you, keep calm and do what needs to be done. Keep prospecting, don’t stop. Also, remember that it’s darkest and coldest right before dawn … and that there are no such things as coincidences.

This client was a huge win for me! Not only did it help restore my finances, it also restored my confidence! It also added some much-needed stability to my business as we turned project work into a monthly retainer agreement.

This client also gave me the income predictability I would need a few months later, when Steve Slaunwhite, Pete Savage and I landed a book deal from Penguin to write The Wealthy Freelancer. Writing that book required a significant amount of time. So, having a steady anchor client made a big difference.

Transitioning Into Part-Time Coaching and Training

I spent a great part of 2010 promoting The Wealthy Freelancer and rebuilding my coaching and training business for freelancers. Pete, Steve and I partnered on this venture, which evolved into International Freelancers Academy. But this time around, I was much smarter about the risks I took. I kept three to four steady copywriting clients.

In early 2011 Pete stepped aside to refocus on his freelance business. But I decided to stick with International Freelancers Academy. I couldn’t deny it: I loved writing for clients … but I LOVED teaching and coaching. I found that I had a unique perspective to share with new and experienced freelancers. I recognized that I was a student of the process and had a talent for teaching and training from experience.

Over the next 18 months, I made a conscious decision to transition into teaching, coaching and training freelancers nearly full time. Not 100%, but maybe 80% to 90% of my time, energy and attention. I still wanted to keep a couple of clients. Why?

Because I still love writing content and copy for corporate clients.

Because I feel it’s good to keep one foot in the business at all times.

International Freelancers Academy broke six figures in revenue in 2011. It required 80% of my time but provided only 20% of my income.

2012 was another six-figure year, but this time profits were a bit higher. That’s the year I decided to make a big and sudden shift in my mix of freelancing vs. coaching/training time. Within a few months I went from 80% freelancing to about 80% coaching/training.

It was scary at first. But trying to do this gradually was not working. In order to make it happen, I had to make a few big and bold moves.

The difference between 2008 and 2012 in my attempt to launch a side business is that in 2008, I lost sight of what was important. I made decisions foolishly and ignored my main source of income, which was freelance work. This time around, I made my decisions from a much better vantage point. I had the scar tissue. I had grown personally and professionally. I was more confident and much more strategic.

What Do I Do Today?

Approximately 85% of my income comes from coaching/training and from publishing educational, results-driven programs.

I still have two to three relatively small freelance clients for which I write white papers, case studies, articles and web copy. I love that kind of work, as long as it’s with the right kinds of clients!

The decision to change the nature of my business came from the realization that I have a true passion for teaching and helping other freelancers succeed. A big part of this has to do with my own struggles to build a successful business under great pressure.

I’ve since learned that I’m wired to take apart situation, analyze it and show others what went right and what went wrong. I’m obsessed with this concept of paving the way for others; with making it easier for others to succeed. And I want to do as much of this kind of work as possible.

I also love to build and grow businesses. The Academy and this B2B Business Launcher venture gives me the opportunity to do this in a way that’s true to me and to who I am.

Key lesson: If you’re going to start a sideline, do it on something you love. Something you’re passionate about. Do NOT just do it for the money. Why? Because when the going gets tough, you’ll quit if money is your main motivator. I would do this for FREE if I were financially independent! That’s my litmus test.

How would I summarize my last 10 years in business?

Find what you love, what makes you come alive. And do more of that.

Follow your bliss. Even if it involves taking big risks and working harder than you’ve ever worked.

I’ll leave you with a beautiful poem by Guillaume Apollinaire. It sums up this idea better I can…

“Come to the edge,” he said.They said, “We are afraid.”“Come to the edge,” he said.They came.He pushed them.And they flew.

Momentum … Finally!

By the fall of 2005, I was consistently earning $2k – $3k a month part time. I was sending all after-tax dollars to savings.

I was extremely busy, working at least 4 nights/week + all Saturdays.

By early 2006, things were now out of control. I often worked 7 days a week and pulled an all-nighter every 2 or 3 weeks in order to meet client deadlines. Fortunately, I was getting close to my savings goal.

Then, something wonderful happened: my employer got acquired by a larger company. They offered me to stay in my current position, which I accepted … but only because I wanted to wait to cash in my stock options.

I began the health insurance application and underwriting process (there was no point in starting earlier). All went through OK, which was a great relief, because securing affordable health insurance was my last hurdle. I had the savings. I had the steady stream of clients and projects, I was making enough on a part-time basis that I knew that if I could just take my business full time, I would be fine.

But the weekend before I was going to turn in my notice … I got cold feet! I asked my wife if she thought I was making the right decision. She urged me to revisit my reasons for going solo. And that gave me the clarity I needed to move forward.

Key lesson: When in doubt, always go back to your core reasons for going out on your own. What’s your Big Why? Always have a solid “Why” that’s not just about the money. Because when you do, you’ll push through the tough times, and you’ll have a real, fundamental reason to get up every day.

Let’s Get This Message Out There

Want to get more tips and strategies for boosting your writing income? There are three ways you can enjoy these tips and strategies — and a couple of ways you can help me grow the movement to banish the “starving writer” syndrome: